Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes

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URI: http://hdl.handle.net/10347/17410
ISSN: 2155-5435
DOI: 10.1021/acscatal.8b01296

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2018-06-04

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American Chemical Society
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Abstract

We report a highly enantioselective [3C + 2C] intramolecular cycloaddition of alkylidenecyclopropanes (ACPs) and alkenes. The best results are obtained by using sterically demanding chiral phosphoramidite ligands derived from Vapol. Moreover, we also show that related, but less bulky, phosphoramidites can also lead to very effective [4C + 3C] cycloadditions when dienes, instead of alkenes, are used as reacting partners. The reactions provide a practical, simple, and selective access to optically active, synthetically appealing 5,5- and 5,7-bicyclic systems

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NOTICE: This is the peer reviewed version of the following article: Felipe Verdugo, Lara Villarino, Juan Durán, Moisés Gulías, José L. Mascareñas and Fernando López (2018), Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intra-molecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 2018, 8, 6100–6105 [DOI: 10.1021/acscatal.8b01296]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving

Keywords

Alkylidenecyclopropane| Asymmetric| Cycloaddition| Enantioselective| Palladium| Phosphoramidite

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Verdugo, F., Villarino, L., Durán, J., Gulías, M., Mascareñas, J., & López, F. (2018). Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 8(7), 6100-6105. doi: 10.1021/acscatal.8b01296

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This work received financial support from the spanish MINECO grants (Nos. SAF2016-76689-R, CTQ2016-77047-P, CTQ2017-84767-P, FPU to L.V. and J.D.), Xunta de Galicia (Nos. ED431C 2017/19, 2015-CP082, and Centro Singular de Investigación de Galicia accreditation 2016-2019 ED431G/09), the ERDF and ERC (Adv. Grant No. 340055). The Orfeo-Cinqa network CTQ2016-81797-REDC, CONICYT-Becas Chile (Ph.D. grant to F.V.) and Sarah Walker (preliminary work) are also acknowledged

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© 2018 American Chemical Society

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